Possible Clues:

• His mom's first name was Stanley
• 'Dreams of My Father' memoirist
• Hawaii-born U.S. president
• Noted 1991 Harvard Law grad
• President in 2014's Tan Suit Gate
• Barack --, the 44th President of the United States
• Two-time Best Spoken Word Album Grammy winner
• Head of state getting round more than half the state
• President whose first name means 'one who is blessed'
• Time's second African-American Person of the Year